Toluene → HCID 86718845, compound

HRID 1523228Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:20][C@H:21]1[C@@H:25]2[O:26][C:27]([CH3:30])([CH3:29])[O:28][C@@H:24]2[C@@H:23]([OH:31])[CH2:22]1.C1(C)C=CC=CC=1>C(O)(C)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]([O-:19])=[O:18])=[O:7])([CH3:4])([CH3:2])[CH3:3].[OH:31][C@@H:23]1[C@H:24]2[O:28][C:27]([CH3:29])([CH3:30])[O:26][C@H:25]2[C@H:21]([NH3+:20])[CH2:22]1

Participants

Conditions

Temperature: 63 °C

Procedure

N-(tert-Butoxycarbonyl)-L-phenylalanine (4.1 g, 99%, 15.2 mmol), (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (2.6 g, 96%, 14.5 mmol), toluene (1.5 mL) and iso-propanol (19.5 mL) were taken to a flask with a stirrer. The mixture was heated under stirring to 63° C. when a clear solution was obtained. The solution was cooled and crystallization started at 53° C. The slurry was further cooled to 0° C. and stirred at this temperature for 60 min. The crystals were isolated on a glass filter, washed with cooled iso-propanol (17.5 mL) and dried in vacuum at 40° C. to give an amount of 2.73 g. The assay by titration was 99.7% and ee by LC 98.8%. The yield was 42.7%.

Workup

temperatureThe mixture was heated
customwas obtained
temperatureThe solution was cooled
customcrystallization
customstarted at 53° C
temperatureThe slurry was further cooled to 0° C.
stirringstirred at this temperature for 60 min
customThe crystals were isolated on a glass
filtrationfilter
washwashed with cooled iso-propanol (17.5 mL)
customdried in vacuum at 40° C.
customto give an amount of 2.73 g

Sources & evidence

ORD record: ord-da0cd6bc78ad4b93b44e04ff916850f6
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079873B2

Reaction notes

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